N-Substituted dichloromaleimides, and anti-bacterial and fungicidal use thereof

ABSTRACT

New N-substituted dichloromaleimides of the general formula (I) ##STR1## in which R stands for hydrogen or alkyl 
     Ar stands for optionally substituted aryl, 
     A 1  and A 2  independently of one another each stand for optionally substituted alkylene and 
     n stands for a number 0 or 1, 
     with the exception of the compound 2-(dichloromaleimido)acetanilide, have been found. These compounds are useful as pesticides, especially as fungicides and bactericides.

The invention relates to new N-substituted dichloromaleimides, a processto the preparation thereof, and their use as pesticides.

It is known that certain dicarboximides, such as, for example, thecompound N-trichloromethanesulphenylphthalimides (folpet) or thecompound N-trichloromethanesulphenyl-tetrahydrophthalimide (captan) havea good fungicidal activity (cf., for example, K. H. Buchel,"Pflanzenaschutz and Schadlingsbekampfung" [Plant Protection and PestControl], p. 140, Thieme Verlag Stuttgart 1977).

However, the activity of these known compounds is not completelysatisfactory in all fields of applications, in particular at lowapplication rates and concentrations.

Furthermore, the compound 2-(dichloromaleimidoacetanilide has beendisclosed (cf. FR 2,005,669). Nothing was known hitherto about anactivity of this compound against pests.

New N-substituted dichloromaleimides of the general formula (I) ##STR2##in which R stands for hydrogen or alkyl,

Ar stands for optionally substituted aryl,

A¹ and A² independently of one another each stand for optionallysubstituted alkylene and

n stands for a number 0 or 1,

with the exception of the compound 2-(dichloromaleimido)-acetanilide,have been found.

Depending on the type of the substituents A¹ and/or A², the compounds ofthe formula (I) may be present as optical isomers or isomer mixtures ofvarying composition. Both the pure isomers and the isomer mixtures areclaimed according to the invention.

Furthermore, it has been found that the new N-substituteddichloromaleimides of the general formula (I) ##STR3## in which R standsfor hydrogen or alkyl,

Ar stands for optionally substituted aryl,

A¹ and A² independently of one another each stand for optionallysubstituted alkylene and

n stands for a number 0 or 1,

with the exception of the compound 2-(dichloromaleimido)-acetanilide,are obtained when dichloromaleimidocarbonyl halides of the formula (II)##STR4## in which A¹ has the abovementioned meaning and

Hal stands for halogen,

are reacted with amines of the formula (III) ##STR5## in which R, Ar, A²and n have the abovementioned meaning, if appropriate in the presence ofa diluent and if appropriate in the presence of an acid-binding agent.

Finally, it has been found that the new N-substituted dichloromaleimidesof the general formula (I) have a good action against pests.

Surprisingly, the N-substituted dichloromaleimides of the formula (I)according to the invention show a considerably better fungicidalactivity than the dicarboximides known from the prior art, such as, forexample, the compound N-trichloromethanesulphenylphthalimide (folpet) orthe compound N-trichloromethanesulphenyl-tetrahydrophthalimide (captan),which are chemically similar compounds of a similar type of action.

Formula (I) provides a general definition of the N-substituteddichloromaleimides according to the invention. Preferred compounds ofthe formula (I) are those in which

R stands for hydrogen or for straight-chain or branched alkyl having 1to 6 carbon atoms,

Ar stands for phenyl which is optionally monosubstituted orpolysubstituted by identical or different substituents, suitablesubstituents being: halogen, cyano, nitro, in each case straight-chainor branched alkyl, alkoxy or alkylthio, each having 1 to 4 carbon atoms,in each case straight-chain or branched halogenoalkyl, halogenoalkoxy,dioxyhalogenoalkylene or halogenoalkylthio, each having 1 to 4 carbonatoms and 1 to 9 identical or different halogen atoms, in each casestraight-chain or branched alkenyl, alkinyl, alkenyloxy or alkinyloxy,each having 3 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms,in each case straight-chain or branched alkoxycarbonylalkyl oralkoxyalkyl, each having 1 to 4 carbon atoms in the individual alkylmoieties, or phenyl, benzyl, phenoxy or benzyloxy, each optionallymonosubstituted or polysubstituted by identical or differentsubstituents from the series comprising halogen and/or straight-chain orbranched alkyl having 1 to 4 carbon atoms,

A¹ and A² independently of one another each stand for optionallyphenyl-substituted, straight-chain or branched alkylene having 1 to 8carbon atoms, where the phenyl substituent can optionally bemonosubstituted or polysubstituted by identical or differentsubstituents from the series comprising: halogen, in particularfluorine, chlorine or bromine, in each case straight-chain or branchedalkyl, alkoxy, halogenoalkyl or halogenoalkoxy, each having 1 to 4carbon atoms, and, in the case of halogenoalkyl or halogenoalkoxy,having 1 to 9 identical or different halogen atoms, and

n stands for a number 0 or 1,

with the exception of the compound 2-(dichloromaleimido)-acetanilide.

Very particularly preferred compounds of the formula (I) are those inwhich

R stands for hydrogen or for straight-chain or branched alkyl having 1to 4 carbon atoms,

Ar stands for phenyl which is optionally monosubstituted topentasubstituted by identical or different substituents, suitablesubstituents being: fluorine, chlorine, bromine, cyano, nitro, methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- ori-propoxy, methylthio, trifluoromethyl, trifluoromethoxy,dioxydifluoromethylene, trifluoromethylthio, allyl, propargyl,cyclopropyl, cyclohexyl, phenyl, benzyl, phenoxy or benzyloxy,

A¹ stands for straight-chain or branched alkylene which is optionallymonosubstituted by phenyl and which has 1 to 6 carbon atoms,

A² stands for unsubstituted straight-chain or branched alkylene having 1to 6 carbon atoms and

n stands for a number 0 or 1,

with the exception of the compound 2-(dichloromaleimido)-acetanilide.

Very particularly preferred compounds of the formula (I) are those inwhich

R stands for hydrogen, methyl or ethyl,

Ar stands for phenyl which is optionally monosubstituted, disubstitutedor trisubstituted by identical or different substituents, suitablesubstituents being: fluorine, chlorine, bromine, cyano, nitro, methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, methylthio,trifluoromethyl, trifluoromethoxy, trifluoromethylthio or divalentdioxydifluoromethylene,

A¹ stands for straight-chain or branched alkylene which is optionallymonosubstituted by phenyl and which has 1 to 4 carbon atoms,

A² stands for straight-chain or branched alkylene having 1 to 4 carbonatoms and

n stands for a number 0 or 1,

with the exception of the compound 2-(dichloromaleimido)-acetanilide.

In addition to the compounds mentioned in the preparation examples, thefollowing N-substituted dichloromaleimides of the general formula (I)may be mentioned individually:

    ______________________________________                                         ##STR6##                      (I)                                            A.sup.1     R     (A.sup.2).sub.n                                                                          Ar                                               ______________________________________                                        CH.sub.2    H     --                                                                                        ##STR7##                                        CH.sub.2    H     --                                                                                        ##STR8##                                        CH.sub.2    H     CH.sub.2                                                                                  ##STR9##                                        CH.sub.2    H     (CH.sub.2).sub.4                                                                          ##STR10##                                       CH.sub.2    H     (CH.sub.2).sub.6                                                                          ##STR11##                                       CH.sub.2    H     CH.sub.2                                                                                  ##STR12##                                       CH.sub.2    H     CH.sub.2                                                                                  ##STR13##                                       CH.sub.2    H     (CH.sub.2).sub.3                                                                          ##STR14##                                       CH.sub.2    H     (CH.sub.2).sub.5                                                                          ##STR15##                                       (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR16##                                       (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR17##                                       (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR18##                                       CH.sub.2    H     --                                                                                        ##STR19##                                       CH.sub.2    H     --                                                                                        ##STR20##                                       CH.sub.2    H     --                                                                                        ##STR21##                                       CH.sub.2    H     --                                                                                        ##STR22##                                       CH.sub.2    H     --                                                                                        ##STR23##                                       CH.sub.2    H     --                                                                                        ##STR24##                                       CH.sub.2    H     --                                                                                        ##STR25##                                       CH.sub.2    H     --                                                                                        ##STR26##                                       CH.sub.2    H     --                                                                                        ##STR27##                                       CH.sub.2    H     CH.sub.2                                                                                  ##STR28##                                       CH.sub.2    H     CH.sub.2                                                                                  ##STR29##                                       CH.sub.2    H     CH.sub.2                                                                                  ##STR30##                                       CH.sub.2    H     (CH.sub.2).sub.2                                                                          ##STR31##                                       CH.sub.2    H     (CH.sub.2).sub.2                                                                          ##STR32##                                       CH.sub.2    H     (CH.sub.2).sub.2                                                                          ##STR33##                                       (CH.sub.2).sub.2                                                                          H     --                                                                                        ##STR34##                                       (CH.sub.2).sub.2                                                                          H     --                                                                                        ##STR35##                                       (CH.sub.2).sub.2                                                                          H     --                                                                                        ##STR36##                                       (CH.sub.2).sub.2                                                                          H     --                                                                                        ##STR37##                                       (CH.sub.2).sub.2                                                                          H     --                                                                                        ##STR38##                                       (CH.sub.2).sub.2                                                                          H     --                                                                                        ##STR39##                                       (CH.sub.2).sub.2                                                                          H     --                                                                                        ##STR40##                                       (CH.sub.2).sub.2                                                                          H     --                                                                                        ##STR41##                                       (CH.sub.2).sub.2                                                                          H     --                                                                                        ##STR42##                                       (CH.sub.2).sub.2                                                                          H     CH.sub.2                                                                                  ##STR43##                                       (CH.sub.2).sub.2                                                                          H     CH.sub.2                                                                                  ##STR44##                                       (CH.sub.2).sub.2                                                                          H     CH.sub.2                                                                                  ##STR45##                                       (CH.sub.2).sub.2                                                                          H     (CH.sub.2).sub.2                                                                          ##STR46##                                       (CH.sub.2).sub.2                                                                          H     (CH.sub.2).sub.2                                                                          ##STR47##                                       (CH.sub.2).sub.2                                                                          H     (CH.sub.2).sub.2                                                                          ##STR48##                                       (CH.sub.2).sub.3                                                                          H     --                                                                                        ##STR49##                                       (CH.sub.2).sub.3                                                                          H     --                                                                                        ##STR50##                                       (CH.sub.2).sub.3                                                                          H     --                                                                                        ##STR51##                                       (CH.sub.2).sub.3                                                                          H     --                                                                                        ##STR52##                                       (CH.sub.2).sub.3                                                                          H     --                                                                                        ##STR53##                                       (CH.sub.2).sub.3                                                                          H     --                                                                                        ##STR54##                                       (CH.sub.2).sub.3                                                                          H     --                                                                                        ##STR55##                                       (CH.sub.2).sub.3                                                                          H     --                                                                                        ##STR56##                                       (CH.sub.2).sub.3                                                                          H     --                                                                                        ##STR57##                                       (CH.sub.2).sub.3                                                                          H     CH.sub.2                                                                                  ##STR58##                                       (CH.sub.2).sub.3                                                                          H     CH.sub.2                                                                                  ##STR59##                                       (CH.sub.2).sub.3                                                                          H     CH.sub.2                                                                                  ##STR60##                                       (CH.sub.2).sub.3                                                                          H     (CH.sub.2).sub.2                                                                          ##STR61##                                       (CH.sub.2).sub.3                                                                          H     (CH.sub.2).sub.2                                                                          ##STR62##                                       (CH.sub.2).sub.3                                                                          H     (CH.sub.2).sub.2                                                                          ##STR63##                                        ##STR64##  H     --                                                                                        ##STR65##                                        ##STR66##  H     --                                                                                        ##STR67##                                        ##STR68##  H     --                                                                                        ##STR69##                                        ##STR70##  H     --                                                                                        ##STR71##                                        ##STR72##  H     --                                                                                        ##STR73##                                        ##STR74##  H     --                                                                                        ##STR75##                                        ##STR76##  H     --                                                                                        ##STR77##                                        ##STR78##  H     --                                                                                        ##STR79##                                        ##STR80##  H     --                                                                                        ##STR81##                                        ##STR82##  H     CH.sub.2                                                                                  ##STR83##                                        ##STR84##  H     CH.sub.2                                                                                  ##STR85##                                        ##STR86##  H     CH.sub.2                                                                                  ##STR87##                                        ##STR88##  H     (CH.sub.2).sub.2                                                                          ##STR89##                                        ##STR90##  H     (CH.sub.2).sub.2                                                                          ##STR91##                                        ##STR92##  H     (CH.sub.2).sub.2                                                                          ##STR93##                                        ##STR94##  H     --                                                                                        ##STR95##                                        ##STR96##  H     --                                                                                        ##STR97##                                        ##STR98##  H     --                                                                                        ##STR99##                                        ##STR100## H     --                                                                                        ##STR101##                                       ##STR102## H     --                                                                                        ##STR103##                                       ##STR104## H     --                                                                                        ##STR105##                                       ##STR106## H     --                                                                                        ##STR107##                                       ##STR108## H     --                                                                                        ##STR109##                                       ##STR110## H     --                                                                                        ##STR111##                                       ##STR112## H     CH.sub.2                                                                                  ##STR113##                                       ##STR114## H     CH.sub.2                                                                                  ##STR115##                                       ##STR116## H     CH.sub.2                                                                                  ##STR117##                                       ##STR118## H     (CH.sub.2).sub.2                                                                          ##STR119##                                       ##STR120## H     (CH.sub.2).sub.2                                                                          ##STR121##                                       ##STR122## H     (CH.sub.2).sub.2                                                                          ##STR123##                                       ##STR124## H     --                                                                                        ##STR125##                                       ##STR126## H     --                                                                                        ##STR127##                                       ##STR128## H     --                                                                                        ##STR129##                                       ##STR130## H     --                                                                                        ##STR131##                                       ##STR132## H     --                                                                                        ##STR133##                                       ##STR134## H     --                                                                                        ##STR135##                                       ##STR136## H     --                                                                                        ##STR137##                                       ##STR138## H     --                                                                                        ##STR139##                                       ##STR140## H     --                                                                                        ##STR141##                                       ##STR142## H     CH.sub.2                                                                                  ##STR143##                                       ##STR144## H     CH.sub.2                                                                                  ##STR145##                                       ##STR146## H     CH.sub.2                                                                                  ##STR147##                                       ##STR148## H     (CH.sub.2).sub.2                                                                          ##STR149##                                       ##STR150## H     (CH.sub.2).sub.2                                                                          ##STR151##                                       ##STR152## H     (CH.sub.2).sub.2                                                                          ##STR153##                                       ##STR154## H     --                                                                                        ##STR155##                                       ##STR156## H     --                                                                                        ##STR157##                                       ##STR158## H     --                                                                                        ##STR159##                                       ##STR160## H     --                                                                                        ##STR161##                                       ##STR162## H     --                                                                                        ##STR163##                                       ##STR164## H     --                                                                                        ##STR165##                                       ##STR166## H     --                                                                                        ##STR167##                                       ##STR168## H     --                                                                                        ##STR169##                                       ##STR170## H     --                                                                                        ##STR171##                                       ##STR172## H     CH.sub.2                                                                                  ##STR173##                                       ##STR174## H     CH.sub.2                                                                                  ##STR175##                                       ##STR176## H     CH.sub.2                                                                                  ##STR177##                                       ##STR178## H     (CH.sub.2).sub.2                                                                          ##STR179##                                       ##STR180## H     (CH.sub.2).sub.2                                                                          ##STR181##                                       ##STR182## H     (CH.sub.2).sub.2                                                                          ##STR183##                                       ##STR184## H     --                                                                                        ##STR185##                                       ##STR186## H     --                                                                                        ##STR187##                                       ##STR188## H     --                                                                                        ##STR189##                                       ##STR190## H     --                                                                                        ##STR191##                                       ##STR192## H     --                                                                                        ##STR193##                                       ##STR194## H     --                                                                                        ##STR195##                                       ##STR196## H     --                                                                                        ##STR197##                                       ##STR198## H     --                                                                                        ##STR199##                                       ##STR200## H     --                                                                                        ##STR201##                                       ##STR202## H     CH.sub.2                                                                                  ##STR203##                                       ##STR204## H     CH.sub.2                                                                                  ##STR205##                                       ##STR206## H     CH.sub.2                                                                                  ##STR207##                                       ##STR208## H     (CH.sub.2).sub.2                                                                          ##STR209##                                       ##STR210## H     (CH.sub.2).sub.2                                                                          ##STR211##                                       ##STR212## H     (CH.sub.2).sub.2                                                                          ##STR213##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR214##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR215##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR216##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR217##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR218##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR219##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR220##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR221##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR222##                                      (CH.sub.2).sub.4                                                                          H     CH.sub.2                                                                                  ##STR223##                                      (CH.sub.2).sub.4                                                                          H     CH.sub.2                                                                                  ##STR224##                                      (CH.sub.2).sub.4                                                                          H     CH.sub.2                                                                                  ##STR225##                                      (CH.sub.2).sub.4                                                                          H     (CH.sub.2).sub.2                                                                          ##STR226##                                      (CH.sub.2).sub.4                                                                          H     (CH.sub.2).sub.2                                                                          ##STR227##                                      (CH.sub.2).sub.4                                                                          H     (CH.sub.2).sub.2                                                                          ##STR228##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR229##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR230##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR231##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR232##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR233##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR234##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR235##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR236##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR237##                                      (CH.sub.2).sub.5                                                                          H     CH.sub.2                                                                                  ##STR238##                                      (CH.sub.2).sub.5                                                                          H     CH.sub.2                                                                                  ##STR239##                                      (CH.sub.2).sub.5                                                                          H     CH.sub.2                                                                                  ##STR240##                                      (CH.sub.2).sub.5                                                                          H     (CH.sub.2).sub.2                                                                          ##STR241##                                      (CH.sub.2).sub.5                                                                          H     (CH.sub.2).sub.2                                                                          ##STR242##                                      (CH.sub.2).sub.5                                                                          H     (CH.sub.2).sub.2                                                                          ##STR243##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR244##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR245##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR246##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR247##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR248##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR249##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR250##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR251##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR252##                                      (CH.sub.2).sub.6                                                                          H     CH.sub.2                                                                                  ##STR253##                                      (CH.sub.2).sub.6                                                                          H     CH.sub.2                                                                                  ##STR254##                                      (CH.sub.2).sub.6                                                                          H     CH.sub.2                                                                                  ##STR255##                                      (CH.sub.2).sub.6                                                                          H     (CH.sub.2).sub.2                                                                          ##STR256##                                      (CH.sub.2).sub.6                                                                          H     (CH.sub.2).sub.2                                                                          ##STR257##                                      (CH.sub.2).sub.6                                                                          H     (CH.sub.2).sub.2                                                                          ##STR258##                                       ##STR259## H     --                                                                                        ##STR260##                                       ##STR261## H     --                                                                                        ##STR262##                                       ##STR263## H     --                                                                                        ##STR264##                                       ##STR265## H     --                                                                                        ##STR266##                                       ##STR267## H     --                                                                                        ##STR268##                                       ##STR269## H     --                                                                                        ##STR270##                                       ##STR271## H     --                                                                                        ##STR272##                                       ##STR273## H     --                                                                                        ##STR274##                                       ##STR275## H     --                                                                                        ##STR276##                                       ##STR277## H     CH.sub.2                                                                                  ##STR278##                                       ##STR279## H     CH.sub.2                                                                                  ##STR280##                                       ##STR281## H     CH.sub.2                                                                                  ##STR282##                                       ##STR283## H     (CH.sub.2).sub.2                                                                          ##STR284##                                       ##STR285## H     (CH.sub.2).sub.2                                                                          ##STR286##                                       ##STR287## H     (CH.sub.2).sub.2                                                                          ##STR288##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR289##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR290##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR291##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR292##                                      (CH.sub.2).sub.5                                                                          H     --                                                                                        ##STR293##                                      (CH.sub.2).sub.5                                                                          H     CH.sub.2                                                                                  ##STR294##                                      (CH.sub.2).sub.5                                                                          H     CH.sub.2                                                                                  ##STR295##                                      (CH.sub.2).sub.5                                                                          H     (CH.sub.2).sub.2                                                                          ##STR296##                                      (CH.sub.2).sub.5                                                                          H     (CH.sub.2).sub.2                                                                          ##STR297##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR298##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR299##                                      (CH.sub.2).sub.4                                                                          H     --                                                                                        ##STR300##                                      (CH.sub.2).sub.4                                                                          H     (CH.sub.2).sub.2                                                                          ##STR301##                                      (CH.sub.2).sub.4                                                                          H     (CH.sub.2).sub.2                                                                          ##STR302##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR303##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR304##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR305##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR306##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR307##                                      (CH.sub.2).sub.6                                                                          H     --                                                                                        ##STR308##                                      (CH.sub.2).sub.6                                                                          H     CH.sub.2                                                                                  ##STR309##                                      (CH.sub.2).sub.6                                                                          H     CH.sub.2                                                                                  ##STR310##                                      (CH.sub.2).sub.6                                                                          H     (CH.sub.2).sub.2                                                                          ##STR311##                                      (CH.sub.2).sub.6                                                                          H     (CH.sub.2).sub.2                                                                          ##STR312##                                      (CH.sub.2).sub.4                                                                          H     CH.sub.2                                                                                  ##STR313##                                      (CH.sub.2).sub.4                                                                          H     CH.sub.2                                                                                  ##STR314##                                       ##STR315## H     --                                                                                        ##STR316##                                       ##STR317## H     --                                                                                        ##STR318##                                       ##STR319## H     --                                                                                        ##STR320##                                       ##STR321## H     --                                                                                        ##STR322##                                       ##STR323## H     --                                                                                        ##STR324##                                       ##STR325## H     --                                                                                        ##STR326##                                       ##STR327## H     --                                                                                        ##STR328##                                       ##STR329## H     CH.sub.2                                                                                  ##STR330##                                       ##STR331## H     --                                                                                        ##STR332##                                       ##STR333## H     (CH.sub.2).sub.2                                                                          ##STR334##                                       ##STR335## H     (CH.sub.2).sub.2                                                                          ##STR336##                                      ______________________________________                                    

If, for example, 2-(dichloromaleimido)-acetyl chloride and3,4,5-trichloroaniline are used as starting substances, the course ofthe reaction of the process according to the invention may berepresented by the following equation: ##STR337##

Formula (II) provides a general definition of thedichloromaleimidocarbonyl halides required as starting substances forcarrying out the process according to the invention. In this formula(II), A¹ preferably stands for those radicals which have already beenmentioned in connection with the description of the substances of theformula (I) according to the invention as being preferred for thissubstituent.

Hal preferably stands for chlorine or bromine.

Some of the dichloromaleimidocarbonyl halides of the formula (II) areknown (cf. CH 617,320 dated 30.05.1980). They are obtained in analogywith known processes when dichloromaleic anhydride of the formula (IV)##STR338## is reacted with amino acids of the formula (V)

    H.sub.2 N--A.sup.1 --COOH                                  (V)

in which

A¹ has the abovementioned meaning, at temperatures between 30° C. and150° C. and if appropriate in the presence of a diluent, such as, forexample, glacial acetic acid, and the resultantdichloromaleimidocarboxylic acids of the formula (VI) ##STR339## inwhich A¹ has the abovementioned meaning, are reacted in a customarymanner with halogenating agents, such as, for example, phosphoruspentachloride, phosphorus tribromide, phosphorus oxychloride or thionylchloride, at temperatures between 30° C. and 150° C.

Most of the dichloromaleimidocarboxylic acids of the formula (VI) areknown (cf. J. Prakt. Chem. 327, 857-864 [1985]).

Dichloromaleic anhydride of the formula (IV) has been disclosed (cf.,for example, DE-OS (German Published Specification) 1,290,555 or U.S.Pat. No. 3,297,722).

Amino acids of the formula (V) are generally known compounds of organicchemistry.

Formula (III) provides a general definition of the amines furthermorerequired as starting substances for carrying out the process accordingto the invention. In this formula (III), R, Ar, A² and n preferablystand for those radicals and indices which have already been mentionedin connection with the description of the substances of the formula (I)according to the invention as being preferred for these substituents andindices.

The amines of the formula (III) are also generally known compounds oforganic chemistry.

Suitable diluents for carrying out the process according to theinvention are inert organic solvents. These include in particularaliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons,such as, for example, benzine, benzene, toluene, xylene, chlorobenzene,petroleum ether, hexane, cyclohexane, dichloromethane, chloroform orcarbon tetrachloride, ethers, such as diethyl ether, dioxane,tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycoldiethyl ether, ketones, such as acetone or butanone, nitriles, such asacetonitrile or propionitrile, amides, such as dimethylformamide,dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide, esters, such as ethyl acetate, orsulphoxides, such as dimethyl sulphoxide.

The process according to the invention is preferably carried out in thepresence of a suitable acid-binding agent. Suitable compounds are allcustomary inorganic or organic bases. These include, for example, alkalimetal hydroxides, such as sodium hydroxide or potassium hydroxide,alkali metal carbonates, such as sodium carbonate, potassium carbonateor sodium hydrogen carbonate, and also tertiary amines, such astriethylamine, N,N-dimethylaniline, pyridine, N,N-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiazabicycloundecene (DBU).

When carrying out the process according to the invention, the reactiontemperatures may be varied within a relatively wide range. In general,the process is carried out at temperatures between 0° C. and 150° C.,preferably at temperatures between 20° C. and 120° C.

For carrying out the process according to the invention, 1.0 to 2.5moles, preferably 1.0 to 1.5 moles, of amine of the formula (III) and ifappropriate 1.0 to 2.5 moles, preferably 1.0 to 1.5 mole, ofacid-binding agent are generally employed per mole ofdichloromaleimidocarbonyl halide of the formula (II). The reaction iscarried out and the reaction products are worked up and isolated bygenerally customary methods.

The active substances according to the invention exhibit a strong actionagainst pests and can be employed in practice for combating undesiredharmful organisms. The active substances can be used as pesticides, inparticular fungicides and bactericides.

Fungicidal agents in plant protection are employed for combatingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericidal agents are employed in plant protection for combatingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some causative organisms of fungal and bacterial diseases which comeunder the generic names listed above may be mentioned as examples, butnot by way of limitation: Xanthomonas species, such as, for example,Xanthomonas campestris pv. oryzae; Pseudomonas species, such as, forexample, Pseudomonas syringae pv. lachrymans; Erwinia species, such as,for example, Erwinia amylovora; Pythium species, such as, for example,Pythium ultimum; Phytophthora species, such as, for example,Phytophthora infestans; Pseudoperonospora species, such as, for example,Pseudoperonospora humuli or Pseudoperonospora cubensis; Plasmoparaspecies, such as, for example, Plasmopara viticola; Peronospora species,such as, for example, Peronospora pisi or P. brassicae; Erysiphespecies, such as, for example, Erysiphe graminis; Sphaerotheca species,such as, for example, Sphaerotheca fuliginiea; Podosphaera species, suchas, for example, Podosphaera leucotrichia; Venturia species, such as,for example, Venturia inaequalis; Pyrenophora species, such as, forexample, Pyrenophora teres or P. graminea (conidia form: Drechslera,syn: Helminthosporium): Cochliobolus species, such as, for example,Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium);Uromyces species, such as, for example, Uromyces appendiculatus;Puccinia species, such as, for example, Puccinia recondita; Tilletiaspecies, such as, for example, Tilletia caries; Ustilago species, suchas, for example, Ustilago nuda or Ustilago avenae; Pellicularia species,such as, for example, Pellicularia sasakii; Pyricularia species, suchas, for example, Pyricularia oryzae; Fusarium species, such as, forexample, Fusarium culmorum; Botrytis species, such as, for example,Botrytis cinerea; Septoria species, such as, for example, Septorianodorum; Leptosphaeria species, such as, for example, Leptosphaerianodorum; Cercospora species, such as, for example, Cercospora canescens;Alternaria species, such as, for example, Alternaria brassicae andPseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The good toleration, by plants, of the active compounds, at theconcentrations required for combating plant diseases, permits treatmentof above-ground parts of plants, of vegetative propagation stock andseeds, and of the soil.

The active compounds according to the invention can be employed withparticularly good success in the combating of diseases in viticulture,fruit growing and vegetable growing, such as, for example, against thecausative organism of powdery mildew of grapevine (Plasmopara viticola)or against the causative organism of apple scab (Venturia inaequalis),or for combating of seed-borne pathogens of soya bean (for exampleRhizoctonia solani, Fusarium sp., Pythium sp.), or for combating of ricediseases, such as, for example, against the causative organism of riceblast disease (Pyricularia oryzae). The systemic properties of thecompounds according to the invention facilitate their application asseed dressing agents.

Furthermore, the active compounds according to the invention alsopossess bactericidal properties.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols, very fine capsules in polymeric substances and in coatingcompositions for seed, as well as ULV cold mist and warm mistformulations.

These formulations are produced in known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is, emulsifying agents and/or dispersingagents, and/or foam-forming agents. In the case of the use of water asan extender, organic solvents can, for example, also be used asauxiliary solvents. As liquid solvents, there are suitable in the main:aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinatedaromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example mineral oil fractions, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water; by liquefied gaseous extenders orcarriers are meant liquids which are gaseous at normal temperature andunder normal pressure, for example aerosol propellants, such ashalogenated hydrocarbons as well as butane, propane, nitrogen and carbondioxide; as solid carriers there are suitable: for example groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly-dispersed silicic acid, alumina and silicates;as solid carriers for granules there are suitable: for example crushedand fractionated natural rocks such as calcite, marble, pumice,sepiolite and dolomite, as well as synthetic granules of inorganic andorganic meals, and granules of organic material such as sawdust, coconutshells, corn cobs and tobacco stalks; as emulsifying and/or foam-formingagents there are suitable: for example non-ionic and anionicemulsifiers, such as polyoxyethylene-fatty acid esters,polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well asalbumin hydrolyzation products; as dispersing agents there are suitable:for example ligninsulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be present in theformulations as a mixture with other known active compounds, such asfungicides, insecticides, acaricides and herbicides, or as a mixturewith fertilizers and growth regulators.

The active compounds can be applied as such, in the form of theirformulations or in use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in the customary manner, forexample by watering, spraying, atomizing, scattering, dusting, foaming,brushing on etc. Furthermore, it is possible to apply the activecompounds using the ultra-low-volume method or to inject the activecompound formulation or the active compound itself into the soil. Theseeds of the plant can also be treated.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range. They are, ingeneral, between 1 and 0.0001% by weight, preferably between 0.5 and0.001%.

In the treatment of seed, amounts of active compound of 0.001 to 50 gper kilogram of seed, preferably 0.01 to 10 g, are generally required.

For the treatment of soil, active compound concentrations of 0.00001 to0.1% by weight, preferably 0.0001 to 0.2% by weight, are required at theplace of action.

PREPARATION EXAMPLES Example 1 ##STR340##

A mixture consisting of 3.5 g (0.027 mol) of p-chloroaniline and 3.45 ml(0.025 mol) of triethylamine in 40 ml of dioxane is added dropwise andwith stirring to 6.0 g (0.025 mol) of 2-chloromaleimidoacetyl chloridein 60 ml of dioxane, during which operation the temperature of thereaction mixture increases to 40° C. When the addition is complete, themixture is stirred at room temperature for 4 hours and poured into 1Nhydrochloric acid, and the resultant precipitate is filtered off bysuction, washed with saturated aqueous sodium hydrogen carbonatesolution and water, and dried at 50° C. in vacuo.

7.1 g (96% of theory) of2-(dichloromaleimido)-N-(4-chlorophenyl)-acetamide of melting point 212°C.-214° C. are obtained.

Preparation of the starting compound Example II-1 ##STR341##

60 ml (0.81 mol) of thionyl chloride are added to 70 g (0.31 mol) of2-(dichloromaleimido)-acetic acid, the mixture is refluxed for 16 hoursand evaporated in vacuo, the residue is taken up in absolute toluene,and the solvent and remaining thionyl chloride are removed in vacuo.

75.1 g (99% of theory) of 2-(dichloromaleimido)acetyl chloride ofmelting point 102° C.-103° C. are obtained.

Example VI-1 ##STR342##

A suspension of 75 g (1.0 mol) of glycine in 400 ml of glacial aceticacid is added to 167 g (1 mol) of dichloromaleic anhydride in 1,000 mlof glacial acetic acid, the mixture is refluxed for one hour and cooled,and the resultant precipitate is filtered off by suction, washed with2.5 l of water and dried at 50° C. in vacuo.

139.9 g (63% of theory) of 2-(dichloromaleimido)-acetic acid of meltingpoint 191° C.-192° C. are obtained.

The following N-substituted dichloromaleimides of the general formula(I) are obtained in a corresponding manner and in accordance with thegeneral instructions for the preparation:

    __________________________________________________________________________     ##STR343##                                    (I)                            Ex-                                                                           No. A.sup.1        R (A.sup.2).sub.n                                                                        Ar          Melting point                       __________________________________________________________________________    2   CH.sub.2       H --                                                                                      ##STR344## 218-220° C.                  3   CH.sub.2       H --                                                                                      ##STR345## 213-215° C.                  4   CH.sub.2       H --                                                                                      ##STR346## 193-194° C.                  5   CH.sub.2       H --                                                                                      ##STR347## 211-213° C.                  6   CH.sub.2       H --                                                                                      ##STR348## 186-188° C.                  7    CH.sub.2      H --                                                                                      ##STR349## 233-235° C.                  8   CH.sub.2       H --                                                                                      ##STR350## 177-178° C.                       ##STR351##    H --                                                                                      ##STR352## 169-171° C.                  10                                                                                 ##STR353##    H --                                                                                      ##STR354## .sup.1 H-NMR*: 4,35-4,45 (1H)       11                                                                                 ##STR355##    H --                                                                                      ##STR356## 89-91° C.                    12                                                                                 ##STR357##    H --                                                                                      ##STR358## 116-118° C.                  13                                                                                 ##STR359##    H --                                                                                      ##STR360## 140-141° C.                  14                                                                                 ##STR361##    H --                                                                                      ##STR362## 70-71° C.                    15                                                                                 ##STR363##    H --                                                                                      ##STR364## .sup.1 H-NMR*: 4,3-4,4 (1H)         16                                                                                 ##STR365##    H --                                                                                      ##STR366## 135-138° C.                  17                                                                                 ##STR367##    H --                                                                                      ##STR368## 146-148° C.                  18  CH.sub.2       CH.sub.3                                                                        --                                                                                      ##STR369## 193-195° C.                  19  CH.sub.2       H --                                                                                      ##STR370## 216° C.                      20  CH.sub.2       H --                                                                                      ##STR371## 208° C.                      21  CH.sub.2       H --                                                                                      ##STR372## 174-177° C.                  22  CH.sub.2       H --                                                                                      ##STR373## 158° C.                      23  CH.sub.2       H --                                                                                      ##STR374## 189-192° C.                  24  CH.sub.2       H --                                                                                      ##STR375## 230° C.                      25  CH.sub.2       H --                                                                                      ##STR376## 220° C.                      26  CH.sub.2       H --                                                                                      ##STR377## 237° C.                      27  CH.sub.2       H --                                                                                      ##STR378## 222° C.                      28  CH.sub.2       H --                                                                                      ##STR379## 213° C.                      29  CH.sub.2       H CH.sub.2                                                                                ##STR380## 173-175° C.                  30  CH.sub.2       H CH.sub.2                                                                                ##STR381## 192-194° C.                  31  CH.sub.2       H --                                                                                      ##STR382## 217-218° C.                  32  CH.sub.2       H CH.sub.2                                                                                ##STR383## 161-163° C.                  33  CH.sub.2       H                                                                                ##STR384##                                                                             ##STR385## 172-173° C.                  34  CH.sub.2       H (CH.sub.2).sub.2                                                                        ##STR386## 170-171° C.                  35  CH.sub.2       H --                                                                                      ##STR387## >220° C.                     36                                                                                 ##STR388##    H --                                                                                      ##STR389## 183- 184° C. (L-Form)        37                                                                                 ##STR390##    H --                                                                                      ##STR391## 235-236° C. (L-Form)         38                                                                                 ##STR392##    H --                                                                                      ##STR393## 183-184° C. (L-Form)         39                                                                                 ##STR394##    H --                                                                                      ##STR395## 178-180° C. (L-Form)         40                                                                                 ##STR396##    H --                                                                                      ##STR397## 199-200° C. (L-Form)         41                                                                                 ##STR398##    H CH.sub.2                                                                                ##STR399## 163-164° C. (L-Form)         42                                                                                 ##STR400##    H CH.sub.2                                                                                ##STR401## 143-144° C. (L-Form)         43  CH.sub.2       H --                                                                                      ##STR402## 206-208° C.                  44  CH.sub.2       H --                                                                                      ##STR403## 206-207° C.                  45  CH.sub.2       H --                                                                                      ##STR404## 194-196° C.                  46  CH.sub.2       H --                                                                                      ##STR405## 180-182° C.                  47  CH.sub.2       H --                                                                                      ##STR406## 204-205° C.                  48  CH.sub.2       H --                                                                                      ##STR407## 180-182° C.                  49  CH.sub.2       H --                                                                                      ##STR408## 208-210°  C.                 50  CH.sub.2       H --                                                                                      ##STR409## 189-190° C.                  51  CH.sub.2       H --                                                                                      ##STR410## 180-182° C.                  52  CH.sub.2       H --                                                                                      ##STR411## 174-176° C.                  53  CH.sub.2       H --                                                                                      ##STR412## 180-182° C.                  54  CH.sub.2       H --                                                                                      ##STR413## 194° C.                      55  CH.sub.2       H --                                                                                      ##STR414## 189-190° C.                  56  CH.sub.2       H --                                                                                      ##STR415## 152° C.                      57  CH.sub.2       H CH.sub.2                                                                                ##STR416## 199° C.                      58  CH.sub.2       H CH.sub.2                                                                                ##STR417## 172° C.                      59  CH.sub.2       H --                                                                                      ##STR418## 230° C.                      60  CH.sub.2       H CH.sub.2                                                                                ##STR419## 181° C.                      61  CH.sub.2       H CH.sub.2                                                                                ##STR420## 184° C.                      62  CH.sub.2       H CH.sub.2                                                                                ##STR421## 210° C.                      63  CH.sub.2       H (CH.sub.2).sub.2                                                                        ##STR422## 179° C.                      64  CH.sub.2       H (CH.sub.2).sub.2                                                                        ##STR423## 185° C.                      65  CH.sub.2       H  (CH.sub.2).sub.2                                                                       ##STR424## 160-162° C.                  66                                                                                 ##STR425##    H CH.sub.2                                                                                ##STR426## 96° C. (L-Form)              67                                                                                 ##STR427##    H CH.sub.2                                                                                ##STR428## 142-143° C. (L-Form)         68                                                                                 ##STR429##    H --                                                                                      ##STR430## 183-184° C.                  69                                                                                 ##STR431##    H --                                                                                      ##STR432## 181° C. (L-Form)             70                                                                                 ##STR433##    H --                                                                                      ##STR434## 159-162° C. (L-Form)         71                                                                                 ##STR435##    H --                                                                                      ##STR436## 194-195° C. (L-Form)         72                                                                                 ##STR437##    H --                                                                                      ##STR438## 65° C. (L-Form)              73  CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR439## 197-198° C.                  74  CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR440## 208-210° C.                  75  CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR441## 188-189° C.                  76  CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR442## 190-191° C.                  77  CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR443## 191° C.                      78  CH.sub.2CH.sub.2                                                                             H CH.sub.2                                                                                ##STR444## 171-172° C.                  79  CH.sub.2CH.sub.2                                                                             H CH.sub.2                                                                                ##STR445## 177-178° C.                  80                                                                                 ##STR446##    H --                                                                                      ##STR447## 173° C. (D,L-Form)           81                                                                                 ##STR448##    H --                                                                                      ##STR449## 168-170° C. (D,L-Form)       82  (CH.sub.2).sub.3                                                                             H --                                                                                      ##STR450## 160-162° C.                  83  CH.sub.2       CH.sub.3                                                                        --                                                                                      ##STR451## 121-122° C.                  84  (CH.sub.2).sub.3                                                                             H --                                                                                      ##STR452## 139-140° C.                  85  (CH.sub.2).sub.3                                                                             H --                                                                                      ##STR453## 166° C.                      86  (CH.sub.2).sub.3                                                                             H --                                                                                      ##STR454## 158° C.                      87  (CH.sub.2).sub.3                                                                             H --                                                                                      ##STR455## 156-158° C.                  88  (CH.sub.2).sub. 3                                                                            H CH.sub.2                                                                                ##STR456## 150-152° C.                  89  (CH.sub.2).sub.3                                                                             H CH.sub.2                                                                                ##STR457## 186-187° C.                  90                                                                                 ##STR458##    H --                                                                                      ##STR459## 201-203° C.                  91                                                                                 ##STR460##    H --                                                                                      ##STR461## 199-200° C.                  92                                                                                 ##STR462##    H --                                                                                      ##STR463## 198° C.                      93                                                                                 ##STR464##    H --                                                                                      ##STR465## 161-163° C.                  94                                                                                 ##STR466##    H --                                                                                      ##STR467## 74-76° C.                    95                                                                                 ##STR468##    H CH.sub.2                                                                                ##STR469## 164° C.                      96                                                                                 ##STR470##    H --                                                                                      ##STR471## 211-212° C. (D,L-Form)       97                                                                                 ##STR472##    H --                                                                                      ##STR473## 219° C. (D,L-Form)           98                                                                                 ##STR474##    H --                                                                                      ##STR475## 181° C. (D,L-Form)           99                                                                                 ##STR476##    H --                                                                                      ##STR477## 182-183° C. (D,L-Form)       100                                                                                ##STR478##    H --                                                                                      ##STR479## 197° C. (D,L-Form)           101                                                                                ##STR480##    H CH.sub.2                                                                                ##STR481## 186-187° C. (D,L-Form)       102                                                                                ##STR482##    H CH.sub.2                                                                                ##STR483## 158° C. (D,L-Form)           103                                                                                ##STR484##    H --                                                                                      ##STR485## 157-158° C.                  104                                                                                ##STR486##    H --                                                                                      ##STR487## 144-146° C.                  105                                                                                ##STR488##    H CH.sub.2                                                                                ##STR489## 145° C.                      106                                                                                ##STR490##    H CH.sub.2                                                                                ##STR491## 190-191° C.                  107 CH.sub.2       H                                                                                ##STR492##                                                                             ##STR493## 175° C.                      108 CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR494## 208-210° C.                  109 CH.sub.2CH.sub.2                                                                             H CH.sub.2CH.sub.2                                                                        ##STR495## 162-164° C.                  110 CH.sub.2CH.sub.2                                                                             H CH.sub.2CH.sub.2                                                                        ##STR496## 131° C.                      111 CH.sub.2CH.sub.2                                                                             H CH.sub.2CH.sub.2                                                                        ##STR497## 159-161° C.                  112 CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR498## 130-131° C.                  113 CH.sub.2CH.sub.2                                                                             H CH.sub.2                                                                                ##STR499## 160° C.                      114 CH.sub.2CH.sub.2                                                                             H CH.sub.2                                                                                ##STR500## 134-137° C.                  115 CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR501## 194° C.                      116 CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR502## 181-183° C.                  117 CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR503## 208° C.                      118 CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR504## 179° C.                      119 (CH.sub.2).sub.3                                                                             H --                                                                                      ##STR505## 132-134° C.                  120 (CH.sub.2).sub.3                                                                             H --                                                                                      ##STR506## 143° C.                      121 (CH.sub.2).sub.3                                                                             H --                                                                                      ##STR507## 80-82° C.                    122  (CH.sub.2).sub.3                                                                            H CH.sub.2                                                                                ##STR508## 126° C.                      123 (CH.sub.2).sub.3                                                                             H CH.sub.2                                                                                ##STR509## 118-120° C.                  124 (CH.sub.2).sub.3                                                                             H --                                                                                      ##STR510## 166-167° C.                  125 CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR511## 183° C.                      126 CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR512## 199-202° C.                  127 CH.sub.2CH.sub.2CH.sub.2                                                                     H --                                                                                      ##STR513## 135° C.                      128 CH.sub.2CH.sub.2CH.sub.2                                                                     H CH.sub.2CH.sub.2                                                                        ##STR514## 132° C.                      129 CH.sub.2CH.sub. 2CH.sub.2                                                                    H --                                                                                      ##STR515## 196° C.                      130 CH.sub.2CH.sub.2CH.sub.2                                                                     H --                                                                                      ##STR516## 176° C.                      131 (CH.sub.2).sub.5                                                                             H --                                                                                      ##STR517## 131--133° C.                 132 (CH.sub.2).sub.5                                                                             H --                                                                                      ##STR518## 149-150° C.                  133 (CH.sub.2).sub.5                                                                             H CH.sub.2                                                                                ##STR519## 130-139° C.                  134                                                                                ##STR520##    H --                                                                                      ##STR521## 146-148° C.                  135                                                                                ##STR522##    H --                                                                                      ##STR523## 160-161° C.                  136 (CH.sub.2 ).sub.4                                                                            H --                                                                                      ##STR524## 156-157° C.                  137 CH.sub.2CH.sub.2                                                                             H --                                                                                      ##STR525## 188° C.                      138 CH.sub.2CH.sub.2CH.sub.2                                                                     H CH.sub.2CH.sub.2                                                                        ##STR526## 139° C.                      139 CH.sub.2CH.sub.2CH.sub.2                                                                     H CH.sub.2CH.sub.2                                                                        ##STR527## 106° C.                      140 CH.sub.2CH.sub.2CH.sub.2                                                                     H --                                                                                      ##STR528## 149° C.                      141 CH.sub.2CH.sub.2CH.sub.2                                                                     H --                                                                                      ##STR529## 128° C.                      142                                                                                ##STR530##    H CH.sub.2                                                                                ##STR531## 171° C.                      143 CH.sub.2CH.sub.2CH.sub.2CH.sub.2                                                             H --                                                                                      ##STR532## 140° C.                      144 CH.sub.2CH.sub.2CH.sub.2CH.sub.2                                                             H CH.sub.2                                                                                ##STR533## 167° C.                      145 CH.sub.2CH.sub.2                                                                             H CH.sub.2                                                                                ##STR534## 177° C.                      146 CH.sub.2CH.sub.2CH.sub.2                                                                     H CH.sub.2                                                                                ##STR535## 132° C.                      147 CH.sub.2CH.sub.2CH.sub.2                                                                     H                                                                                ##STR536##                                                                             ##STR537## 136° C.                      148 CH.sub.2CH.sub.2                                                                             H                                                                                ##STR538##                                                                             ##STR539## 146° C.                      __________________________________________________________________________     *The .sup.1 HNMR spectra wee recorded in deuterochloroform (CDCl.sub.3)       with tetramethylsilane (TMS) as the internal standard. The data of the        chemical shift are expressed as δ-values in ppm.                   

Use Examples

In the following use examples, the compounds listed below were employedas comparison substances: ##STR540##N-Trichloromethanesulphenylphthalimide (folpet) ##STR541##N-Trichloromethanesulphenyltetrahydrophthalimide (captan) Example A

Plasmopara test (vines)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated with an aqueous sporesuspension of Plasmopara viticola and then remain in a humidity chamberat 20° to 22° C. and 100% relative atmospheric humidity for 1 day. Theplants are then placed in a greenhouse at 22° C. and about 80%atmospheric humidity for 5 days. The plants are then moistened andplaced in a humidity chamber for 1 day.

Evaluation is carried out 7 days after the inoculation.

In this test, the compounds of the Preparation Examples 27, 30, 56, 60,77, 79 and 95, for example, show a clearly superior activity as comparedwith the prior art.

Example B Venturia test (apple)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated with an aqueous conidiasuspension of the apple scab causative organism (Venturia inaequalis)and then remain in an incubation cabin at 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at 20° C. and a relativeatmospheric humidity of about 70%.

Evaluation is carried out 12 days after the inoculation.

In this test, the compounds of Preparation Examples 38, 77, 82 and 87,for example, show a clearly superior activity as compared with the priorart.

Example C Pyricularia test (rice)/protective

Solvent: 12.5 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water and the stated amount of emulsifier,to the desired concentration.

To test for protective activity, young rice plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated with an aqueous sporesuspension of Pyricularia oryzae. The plants are then placed in agreenhouse at 100% relative atmospheric humidity and 25° C.

Evaluation of the disease infestation is carried out 4 days after theinoculation.

In this test, the compounds of Preparation Examples 25, 28, 30, 36, 39,42, 64, 74, 75, 76, 79 and 82, for example, show clearly better activityas compared with untreated control plants.

Example D Test for soil-borne pathogens (soya bean)/seed treatment fieldtrial

Amount of seed per plot: 30 g

Plot size: 2 m²

Number of replicates: 3

Development stage of the plants at evaluation: 2-leaf

The active compounds are applied as dry seed-dressing agents. They areprepared by extending the specific active compound with ground naturalminerals to give a finely disperse mixture guaranteeing an evendistribution on the surface of the seeds.

For carrying out the seed-dressing, the infected seeds are shaken for 3minutes in a sealed glass flask together with the seed-dressing agent.

The soil is prepared as is customary in practice, and the seeds are sownin the field at a point in time which is favourable for infection withdisease.

Evaluation is carried out at a point in time when the symptoms ofdiseases are complete and clearly recognizable.

In this test, the compound of Preparation Example 3, for example, has aclearly superior activity as compared with the prior art.

What is claimed is:
 1. An N-substituted dichloromaleimide of the formula##STR542## in which R stands for hydrogen or for alkyl having 1 to 6carbon atoms,Ar stands for unsubstituted phenyl or phenyl which ismono-, di- or tri-substituted by non-sterically hindering identical ordifferent substituents selected from the group consisting of halogen;cyano; nitro; alkyl; alkoxy or alkylthio, each having 1 to 4 carbonatoms; halogenoalkyl, halogenoalkoxy, dioxyhalogenoalkylene orhalogenoalkylthio, each having 1 to 4 carbon atoms and 1 to 9 identicalor different halogen atoms; alkenyl, alkinyl, alkenyloxy or alkinyloxy,each having 3 to 6 carbon atoms; cycloalkyl having 3 to 7 carbon atoms;alkoxycarbonylalkyl or alkoxyalkyl, each having 1 to 4 carbon atoms inthe individual alkyl moieties; phenyl, benzyl, phenoxy, benzyloxy, eachbeing unsubstituted or mono-substituted by substituents selected fromthe group consisting of halogen and alkyl having 1 to 4 carbon atoms, A¹and A² independently of one another each stand for unsubstituted orphenyl-substituted, alkylene having 1 to 8 carbon atoms, where thephenyl substituent is unsubstituted or mono-substituted by substituentsselected from the group consisting of halogen; alkyl, alkoxy,halogenoalkyl or halogenoalkoxy, each having 1 to 4 carbon atoms, and,in the case of halogenoalkyl or halogenoalkoxy, having 1 to 9 identicalor different halogen atoms, and n stands for a number 0 or 1, and pureisomers or isomer mixtures thereof, with the exception of the compound2-(dichloromaleimido)-acetanilide.
 2. An N-substituted dichloromaleimideaccording to claim 1, in whichR stands for hydrogen or for alkyl having1 to 4 carbon atoms, Ar stands for unsubstituted phenyl or phenyl whichis mono-, di- or tri-substituted by identical or differentnon-sterically hindering substituents selected from the group consistingof fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methylthio, trifluoromethyl, trifluoromethoxy, dioxydifluoromethylene,trifluoromethylthio, allyl, propargyl, cyclopropyl, cyclohexyl, phenyl,benzyl, phenoxy and benzloxy, A¹ stands for alkylene which isunsubstituted or substituted by phenyl and which has 1 to 6 carbonatoms, A² stands for unsubstituted alkylene having 1 to 6 carbon atomsand n stands for a number 0 to 1, and pure isomers or isomer mixturesthereof, with the exception of the compound2-(dichloromaleimido)-acetanilide.
 3. An N-substituted dichloromaleimideaccording to claim 1, in whichR stands for hydrogen, methyl or ethyl, Arstands for unsubstituted phenyl or phenyl which is mono-, di-, ortri-substituted by identical or different non-sterically hinderingsubstituents selected rom the group consisting of fluorine, chlorine,bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy,trifluoromethylthio or divalent dioxydifluoromethylene, A¹ stands foralkylene which is unsubstituted or monosubstituted by phenyl and whichhas 1 to 4 carbon atoms, A² stands for alkylene having 1 to 4 carbonatoms and n stands for a number 0 to 1, and pure isomers and isomermixtures thereof, with the exception of the compound2-(dichloromaleimido)-acetanilide.
 4. A compound according to claim 1wherein such compound is2-(dichloromaleimido)-N-(4-methylphenyl)-acetamide of the formula##STR543##
 5. A compound according to claim 1 wherein such compound is2-(dichloromaleimide)-N-(4-methylbenzyl)-acetamide of the formula##STR544##
 6. A compound according to claim 1 wherein such compound is3-(dichloromaleimido)-N-(3,4-dichlorophenyl)-propionamide of the formula##STR545##
 7. A pesticidal composition comprising a pesticidallyeffective amount of at least one N-substituted dichloromaleimideaccording to claim 1, and a suitable extender.
 8. A fungicial orbactericidal composition comprising an effective amount of at least oneN-substituted dichloromaleimide according to claim 1 and a suitableextender.
 9. A method of combating fungi or bacteria comprising applyingto said fungi or bacteria or to a locus thereof an effective amount ofat least one N-substituted-di-chloromaleimide according to claim
 1. 10.A method according to claim 7 wherein such compoundis2-(dichloromaleimido)-N-(4-methylphenyl)-acetamide,2-(dichloromaleimido)-N-(4-methylbenzyl)-acetamide or3-(dichloromaleimido)-N-(3,4-dichlorophenyl)-propionamide.